For me, maintenance became a huge struggle when I had to help my grandfather manage his company as he became too old to keep managing his company, and with my background working logistics at Amazon I realized what a logistical nightmare maintenance was becoming and how much of my time it was eating and hiring additional help is always difficult since I don't know many people with a burning passion for maintenance scheduling, so as good as the work was I always knew it was a temporary hire that could leave at any moment.While reading through here I have to agree that at a certain point having a property manager handle everything from top to bottom is incredibly valuable especially if your intention is passive income.

Fortunately I'm savvy enough to know that would probably be a logistical nightmare, maybe we can team up and do it!  

Not to mention the logistic nightmare of maintaining and convincing the court you're splitting personal expenses from business. 

If anyone can add color please do as I may be incorrect on the logistics here.

Then look at our city profile to figure out the pain in the butt factor of the city or town or village and the other logistical things that could happen.

Logistics aside, I've found it tends to be a sign of some financial chaos in their lives.  

They underestimate the risks in doing so, both because of the logistics of the distance, but also because they misprice the risk in the market and asset they are buying. 

I'm half tempted to try managing it myself for a year but we live two hours away so the logistics of tenant turnover are a concern. 

Let me preface this by saying I am no expert on construction, so I won't be able to give you nearly the same logistical info that the people above have given.

As long as you can later prove that this money did come out of your pocket, no issue.As far as your logistics question, let's flip it and consider it from the buyer's side.